Dimethyl Sulfoxide → HCID 21883599、化合物

HRID 2214861ノート

反応式

HRID 2214861 の反応式
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[C:4]([CH:11]=[O:12])[CH:3]=1.CS(C)=O.[F:17][C:18]([F:27])([F:26])/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>C(OCC)C.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:10][CH:19]([C:18]([F:17])([F:27])[F:26])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]=2[CH:9]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 1229125-Chloro-2-hydroxyisophthalaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

生成物 1

HCID 21883599HCID 21883599、化合物収率 35.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
80 °C

実験手順

A stirred solution of the dialdehyde (Step 2)(1.13 g, 6.14 mmol), dimethyl sulfoxide (6 mL), ethyl 4,4,4-trifluorocrotonate (1.37 mL, 1.55 g, 9.21 mmoL) and triethylamine (1.71 mL, 1.24 g, 12.28 mmol) in a round bottom flask fitted with condenser was heated to 80° C. for 8 h. Upon cooling to room temperature the reaction was diluted with diethyl ether (100 mL) and the resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL), dried over MgSO4, filtered and concentrated in vacuo yielding a tan powder. This powder was taken up in hot hexane-ethyl acetate and filtered to remove insoluble matter. Upon cooling of the filtrate, crystallization followed by vacuum filtration yielded the desired ester as tan crystals (0.726 g, 35%): mp 118.1–119.7° C. This material was of suitable purity to use without further purification.

後処理

  1. temperatureUpon cooling to room temperature the reaction
  2. washthe resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding a tan powder
  7. filtrationfiltered
  8. customto remove insoluble matter
  9. temperatureUpon cooling of the filtrate, crystallization
  10. filtrationfollowed by vacuum filtration

出典と根拠

ORDレコード
ord-6010982e7a724733a4a798379eeda8ef
出典データセット
uspto-grants-2006_09
特許番号
US07109211B2

反応ノート

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